Paul is available for hire
Hire PaulPaul Bennett
Verified Expert in Finance
Management Consulting Expert
Calivigny, Saint George, Grenada
Toptal member since March 18, 2022
Bio
A three-time founder and CEO, board chair, and advisor with a deep background in travel, sustainability, and education, Paul has founded, grown, and exited businesses and now consults with a wide range of executives, founders, and investors. He has deep experience in marketing, building sales teams, technology project and UX management, and strategy, but he also has finance, strategy, and OKR qualifications. Paul is eager to help dynamic organizations grow.
Career Highlights
Board Chair
Sustainable Travel International
Fundraising/Pitch Deck Consultant
Renegade Publishing Inc.
Founder | CEO
Context Travel
Education Highlights
Master's Degree
St. John's College
Bachelor's Degree
Macalester College
Certification Highlights
OKR Master
Udemy
Case Studies
STI Financial Model
Financial ModelingFundraisingModelingManagement ConsultingPrice PositioningBusiness Model Strategy+ 2 more
Pitch Deck and Business Plan for a Startup
FundraisingRevenue & Expense ProjectionsPitch DecksStartupsFinancial ModelingDisruptive Strategy+ 13 more
Product Strategy for Gamified Learning App
Product StrategyUser Experience (UX)WireframingWorkshopsDigital TransformationExecutive Presentations+ 6 more
Software Expertise
- Excel 2016
Other Expertise
- Direct to Consumer (D2C)
- Disruptive Strategy
- Growth
- Modeling
- Objectives & Key Results (OKRs)
- Strategy
- Writing & Editing
Work Experience
Fundraising and Pitch Deck Consultant
2022 - PRESENT
Renegade Publishing Inc.
- Worked on SaaS, digital rights management, and music publishing projects.
- Built a pitch deck and financial model for fundraising.
- Coached the founder on pitching and ran mock sessions.
- Organized an operational plan and built out the finance and HR function.
- Handled ongoing advisory work to help build the business and grow.
Focus areas: Fundraising, Pitch Decks, Fundraising Consultant, Venture Capital, Startups, Growth Strategy Consultants, Competitor Analysis & Profiling, Price Positioning, Total Addressable Market (TAM), United States, Software, Competition Research, Competitive Analysis, Artificial Intelligence (AI), Fundraising Strategy, SaaS, Market Research, Valuation, Music, Music Production, Operational Excellence, Early-stage Startups, Business Planning, Market Research & Analysis, Go-to-market Plans, Software as a Service (SaaS), Organizational Strategy & Design, Innovation, Innovation Strategy, Customer Analysis, Pitch Deck Consultant, Sales Operations
Board Member
2022 - PRESENT
Modern Adventure
- Sat on the board of this innovative travel company that merges experiential marketing with socially-minded travel.
- Advised CEO on fundraising and strategy; helped launch a new product.
- Analyzed a financial model and provided input on the strategic direction.
Focus areas: Management, Strategy, Finance, Governance, Growth, Leadership, Direct to Consumer (D2C), Business Strategy, Business Design, Discovery, Brand Strategy, Growth Strategy, Business Intelligence (BI), Product Development, Growth Strategy Consultants, Price Positioning, United States, Business Services, Fundraising Strategy, Business Development, Market Research, Valuation, Forecasting, Organizational Design, Operational Excellence, Early-stage Startups, Business Planning, Strategic Planning, Food & Beverage, TOM, Market Research & Analysis, Marketing, Go-to-market Plans, Hiring Process Development, Performance Management, Organizational Strategy & Design, Innovation, Innovation Strategy, Customer Analysis, Executive Coaching, CFO, Sales Operations
Founder | CEO
2021 - PRESENT
Cicero Learning
- Built the minimum viable product (MVP) for this startup operating in an emerging education sector.
- Developed the mission, values, and go-to-market strategy.
- Onboarded first clients, held first media appearances, and honed product-market fit.
Focus areas: Startups, Revenue Modeling, Financial Statements, Go-to-market Strategy, Disruptive Strategy, Leadership, Market Sizing, Operations, Branding, Market Research, Direct to Consumer (D2C), Marketing Strategy, eCommerce, Business Design, Business Models, Brand Strategy, Growth Strategy, Pitch Decks, Business Intelligence (BI), Knowledge Management, Product Development, Growth Strategy Consultants, Total Addressable Market (TAM), United States, Software, Artificial Intelligence (AI), Business Services, Marketing Communications (MarCom), Fundraising Strategy, Business Development, Forecasting, Organizational Design, Operational Excellence, Early-stage Startups, Business Planning, Strategic Planning, Food & Beverage, TOM, Market Research & Analysis, Marketplaces, Marketing, Go-to-market Plans, Social Media, Social Media Platforms, Hiring Process Development, Performance Management, Organizational Strategy & Design, Innovation, Innovation Strategy, Customer Analysis, CFO, Pitch Deck Consultant, Sales Operations
Advisor
2019 - PRESENT
Pack Up + Go
- Mentored, advised, and coached the company's young founder as she navigated a new business landscape.
- Helped strategize a new product offering during the COVID-19 pandemic.
- Consulted on building a supply side of the business focused on travel activities.
Focus areas: Operations, Pricing, Branding, Startups, Go-to-market Strategy, Growth, Direct to Consumer (D2C), Human Resources (HR), Digital Transformation, Business Intelligence (BI), Product Development, Growth Strategy Consultants, United States, Business Services, Marketing Communications (MarCom), Forecasting, Organizational Design, Operational Excellence, Early-stage Startups, Business Planning, Strategic Planning, TOM, Market Research & Analysis, Go-to-market Plans, Hiring Process Development, Organizational Strategy & Design, Customer Analysis, Executive Coaching, Pitch Deck Consultant
Advisor
2019 - PRESENT
Portico
- Helped the founder and CEO manage and execute a mergers and acquisitions (M&A) strategy.
- Analyzed a customer acquisition strategy and advised on pricing.
- Provided guidance, mentorship, and coaching to a startup founder navigating a new business.
Focus areas: Mergers & Acquisitions (M&A), Strategy, Startups, Go-to-market Strategy, Growth, Direct to Consumer (D2C), Product Development, Growth Strategy Consultants, Competitor Analysis & Profiling, United States, Software, Competition Research, Business Services, Fundraising Strategy, Sales, Business Development, Valuation, Forecasting, Early-stage Startups, Business Planning, Strategic Planning, TOM, Market Research & Analysis, Marketing, Go-to-market Plans, Software as a Service (SaaS), Hiring Process Development, Organizational Strategy & Design, Innovation, Innovation Strategy, Executive Coaching, Pitch Deck Consultant
Advisor
2019 - PRESENT
BACH
- Assisted the founder and CEO in building a pitch deck and financial model, and raising a series A funding.
- Advised the founder and executive team on a go-to-market strategy targeting travel suppliers.
- Analyzed business development plans and helped create a potential corporate development partnership strategy.
Focus areas: Mentorship, Strategy, Startups, Go-to-market Strategy, Growth, Direct to Consumer (D2C), eCommerce, Product Development, Total Addressable Market (TAM), United States, Competitive Analysis, Business Services, Fundraising Strategy, Early-stage Startups, Business Planning, Strategic Planning, TOM, Marketplaces, Hiring Process Development, Innovation, Executive Coaching, Pitch Deck Consultant
Board Chair
2019 - PRESENT
Sustainable Travel International
- Ran a strategic process that resulted in a transformation of the business from a struggling nonprofit to a growing public benefit corporation involved in solving climate and carbon liability problems in the travel industry and beyond.
- Built a sales function, including recruiting a sales leader and developing a sales strategy.
- Coached the CEO to help her develop her leadership skills.
Focus areas: Strategy, Governance, Finance, Startups, Revenue Modeling, Financial Statements, Go-to-market Strategy, Modeling, Leadership, Objectives & Key Results (OKRs), Market Sizing, Operations, Sustainability, Business Strategy, Marketing Strategy, Change Management, Human Resources (HR), Business Design, Sustainable Advisory, Growth Strategy, Sales Strategy, Digital Transformation, Workshops, Pitch Decks, Product Strategy, Business Intelligence (BI), Executive Presentations, Knowledge Management, Product Development, Growth Strategy Consultants, Competitor Analysis & Profiling, Total Addressable Market (TAM), United States, Competition Research, Artificial Intelligence (AI), Business Services, Marketing Communications (MarCom), SaaS, Sales, Business Development, Market Research, Valuation, Forecasting, Organizational Design, Operational Excellence, Early-stage Startups, Business Planning, Strategic Planning, TOM, Market Research & Analysis, Marketing, Go-to-market Plans, Software as a Service (SaaS), Hiring Process Development, Performance Management, Organizational Strategy & Design, Innovation, Innovation Strategy, Executive Coaching, CFO, Pitch Deck Consultant, Sales Operations
Board Member
2018 - PRESENT
Context Travel
- Sat on the board of directors of this innovative company that I founded and helped build growth.
- Supervised the sustainability strategy of this certified B Corporation.
- Collaborated with the CEO on everything from organizational design to pricing to distribution.
Focus areas: Fundraising, Sustainability, Environmental, Social, and Governance (ESG), Strategy, Startups, Go-to-market Strategy, Governance, Leadership, Mergers & Acquisitions (M&A), Market Research, Business Strategy, Change Management, Human Resources (HR), Business Design, Growth Strategy, Product Strategy, Business Intelligence (BI), Growth Strategy Consultants, Competition Research, Competitive Analysis, Business Services, Fundraising Strategy, Business Development, Valuation, Forecasting, Organizational Design, Operational Excellence, Business Planning, Strategic Planning, TOM, Market Research & Analysis, Marketplaces, Hiring Process Development, Performance Management, Organizational Strategy & Design, Innovation, Innovation Strategy, Sales Operations
Sales Process Expert
2023 - 2023
CAREit Human Technology LLC
- Built a sales strategy to help this startup get traction in the market.
- Performed competitive analysis to understand white spaces and opportunities.
- Wrote a sales playbook that defined the strategy and explored tactics for success.
Focus areas: Sales, Sales Effectiveness, SaaS, Business Development, Market Research, Early-stage Startups, Business Planning, TOM, Market Research & Analysis, Go-to-market Plans, Software as a Service (SaaS), Customer Analysis, Sales Operations
Fundraising/Pitch Deck Consultant
2022 - 2023
Renegade Publishing Inc.
- Worked with the founder/CEO to craft business strategy, including competitive analysis, market sizing, financial modeling, and fundraising plans.
- Built a pitch deck and target list and coached the founder on the pitch, which led to a successful seed round.
- Worked on an operational plan and business services, including IP protection, insurance review, and shepherding the business through a conversion from LLC to C corp.
Focus areas: Fundraising, Pitch Decks, Fundraising Consultant, Venture Capital, Startups, SaaS, Market Research, Early-stage Startups, Business Planning, Market Research & Analysis, Marketing, Go-to-market Plans, Organizational Strategy & Design, Innovation, Innovation Strategy
Founder | CEO
2003 - 2017
Context Travel
- Grew this business from scratch to be the leader in experiential walking tours and a known and respected brand.
- Oversaw every aspect of operations early, focusing specifically on marketing, sales, and growth.
- Recruited a team of top performers across all functions.
- Shepherded the business through a B Corporation certification.
Focus areas: Growth, Leadership, Strategy, Talent Management, Startups, Business Modeling, Revenue Modeling, Financial Statements, Go-to-market Strategy, Disruptive Strategy, Analytics, User Experience (UX), Operations, Pricing, Branding, Due Diligence, Direct to Consumer (D2C), Marketing Strategy, eCommerce, Project Management, Human Resources (HR), Business Design, Business Models, Brand Strategy, Growth Strategy, Sales Strategy, Digital Transformation, Workshops, Product Strategy, Business Intelligence (BI), Executive Presentations, Knowledge Management, Product Development, Growth Strategy Consultants, Competitor Analysis & Profiling, Price Positioning, Total Addressable Market (TAM), United States, Software, Marketing Communications (MarCom), Fundraising Strategy, Sales, Business Development, Market Research, Operational Excellence, Early-stage Startups, Business Planning, Strategic Planning, TOM, Market Research & Analysis, Marketplaces, Marketing, Go-to-market Plans, Social Media, Social Media Platforms, Hiring Process Development, Performance Management, Organizational Strategy & Design, Innovation, Innovation Strategy, Pitch Deck Consultant, Sales Operations
Education
1995 - 1996
Master's Degree in Great Books Program
St. John's College - Santa Fe, New Mexico, United States
1988 - 1992
Bachelor's Degree in Literature
Macalester College - St. Paul, Minnesota, United States
Certifications
OCTOBER 2022 - PRESENT
Strategy Certificate
Harvard Business School
JANUARY 2022 - PRESENT
Financial Modeling and Valuation Analyst (FMVA)®
CFI
FEBRUARY 2019 - PRESENT
OKR Master
Udemy
MARCH 2014 - PRESENT
Google Analytics Certification
Skills
Finance
Financial Modeling, Fundraising, Market Research, Valuation, Forecasting, Revenue Modeling, Business Intelligence (BI), Total Addressable Market (TAM), Mergers & Acquisitions (M&A), Pricing, Due Diligence, Revenue & Expense Projections, Certified Public Accountant (CPA), CFO
Industry Expertise
Early-stage Startups, Software, Music, Food & Beverage, Sustainability, Venture Capital
Geographic Expertise
United States
Output Software
Excel 2016
Other
Disruptive Strategy, Writing & Editing, Strategy, Startups, Direct to Consumer (D2C), Business Strategy, eCommerce, Human Resources (HR), Business Design, Growth Strategy, Sales Strategy, Digital Transformation, Product Development, Growth Strategy Consultants, Competition Research, Fundraising Strategy, Business Development, Organizational Design, Strategic Planning, Market Research & Analysis, Marketplaces, Marketing, Go-to-market Plans, Innovation, Innovation Strategy, Executive Coaching, Google Workspace, Framing Questions, Modeling, Growth, Leadership, Marketing Strategy, Change Management, Project Management, Business Modeling, Go-to-market Strategy, Business Models, Brand Strategy, Management Consulting, Product Strategy, Workshops, Executive Presentations, Knowledge Management, Competitor Analysis & Profiling, Competitive Analysis, Business Services, Marketing Communications (MarCom), Business Model Strategy, Sales, Operational Excellence, Business Planning, Consumer Packaged Goods (CPG), TOM, Hiring Process Development, Performance Management, Organizational Strategy & Design, Customer Analysis, Pitch Deck Consultant, Sales Operations, Slack, Figma, Governance, Finance, Talent Management, Objectives & Key Results (OKRs), Analytics, User Experience (UX), Wireframing, Competitive Intelligence, Market Sizing, Mentorship, Operations, Branding, Environmental, Social, and Governance (ESG), Discovery, Sustainable Advisory, Financial Statements, Management, Pitch Decks, Music Publishing, Fundraising Consultant, Price Positioning, Artificial Intelligence (AI), SaaS, Sales Effectiveness, Music Production, Software as a Service (SaaS), Social Media, Social Media Platforms
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